Structure of 1694-20-8
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Jang, Mingyeong ; Lim, Taeho ; Park, Byoung Yong ; Han, Min Su ;
Abstract: In this study, we developed a metal-free and highly chemoselective method for the reduction of aromatic nitro compounds. This reduction was performed using tetrahydroxydiboron [B2(OH)4] as the reductant and 4,4'-bipyridine as the organocatalyst and could be completed within 5 min at room temperature. Under optimal conditions, nitroarenes with sensitive functional groups, such as vinyl, ethynyl, carbonyl, and halogen, were converted into the corresponding anilines with excellent selectivity while avoiding the undesirable reduction of the sensitive functional groups.
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| CAS No. : | 1694-20-8 |
| Formula : | C14H11NO2 |
| M.W : | 225.24 |
| SMILES Code : | O=[N+](C1=CC=C(/C=C/C2=CC=CC=C2)C=C1)[O-] |
| English Name : | (E)-1-Nitro-4-styrylbenzene |
| MDL No. : | MFCD00053614 |
| InChI Key : | ZISCOWXWCHUSMH-VOTSOKGWSA-N |
| Pubchem ID : | 639659 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 86% | With hydrogen In methanol | |
| With methanol; nickel; ethyl acetate Hydrogenation; | ||
| With hydrogen In ethanol |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 79% | With 18-crown-6 ether; (COCl2)2 In hexane at -10 - -5℃; | |
| With Perbenzoic acid; benzene | ||
| With Perbenzoic acid In chloroform |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 81% | With palladium diacetate; tributyl-amine; sodium carbonate In water at 100℃; for 7h; Yields of byproduct given; | |
| 81% | With palladium diacetate; tributyl-amine; potassium carbonate In water at 100℃; for 7h; | |
| With palladium diacetate; tributyl-amine; sodium carbonate In water at 100℃; other aryl bromides and iodides; other palladium reagents; other bases; var. time; |
| With potassium carbonate In water at 60 - 70℃; for 24h; optical yield given as %de; diastereoselective reaction; | ||
| With potassium carbonate In N,N-dimethyl-formamide at 125℃; for 1h; optical yield given as %de; stereoselective reaction; | ||
| With C17H15F17N2O7PdS; tetrabutylammomium bromide; potassium carbonate In water at 100℃; for 12h; Sealed tube; optical yield given as %de; stereoselective reaction; | ||
| 71.429 % de | With triethylamine; C14H12INPdS2 In N,N-dimethyl-formamide at 105℃; for 5h; Inert atmosphere; Overall yield = > 99 percent; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 80% | With sodium hydroxide In water; acetonitrile at 20℃; for 24h; Irradiation; | |
| 45% | With covalent organic framework constructed from melamine and 2,4,6-triformylphloroglucinol In N,N-dimethyl-formamide at 20℃; for 18h; Irradiation; | |
| With ferrocene In benzene at 25℃; Irradiation; var. of solvent, with and without O2; |
| Irradiation; | ||
| In acetonitrile for 24h; UV-irradiation; Inert atmosphere; | ||
| 12 % de | With (1,3-bis(2,6-di-iso-propylphenyl)imidazol-2-ylidene) (1,10-pehenthroline) copper hexafluorophosphate In dichloromethane at 8 - 20℃; Irradiation; Sealed tube; Green chemistry; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 84% | With iodine In hexane for 1h; Reflux; | Synthesis of 1-15: General procedure: To a solution of benzyl chloride (0.126 g, 1.00 mmol) in dry toluene (7 mL), was added triphenylphosphine (0.313 g, 1.20 mmol) at ambient temperature. The reaction mixture was allowed to reflux for 18 h under N2 atmosphere; during this time the Wittig salt precipitated out, it was filtered, washed and used for further reaction. To a solution of Wittig salt (0.08 g, 0.20 mmol) in CH2Cl2, was added NaOH solution (0.01 g, 0.25 mmol, 3 mL water) at ambient temperature. The solution turned orange red indicating the formation of Wittig ylide. To this solution was added benzaldehyde (0.018 g, 0.16 mmol) and the reaction mixture allowed to stir at ambient temperature for 3 h. The crude product formed was extracted with CH2Cl2, washed with brine and evaporated to dryness. After usual column chromatography (hexane: EtOAc; 9:1), the product obtained was a mixture of cis and trans-isomer, isolated in 87% yield. The above mixture was dissolved in hexane containing catalytic amount of iodine and allowed to reflux for 1 h. The reaction mixture was cooled down to ambient temperature, washed with Na2S2O5 solution and the organic layer evaporated to give pure trans-isomer (1) in quantitative yield (89%) |
| 63% | With <i>N</i>,<i>N</i>-dimethyl-aniline at 25℃; for 24h; | |
| 6% | With aniline at 25℃; for 10h; |
| In decalin at 170℃; further catalysts and temperatures, ΔH(excit.), ΔS(excit.); | ||
| With cyclooctatetraene di-K salt In tetrahydrofuran at -40℃; var. solvents, temp.; other cis-stilbene; | ||
| at 20℃; for 2h; UV-irradiation; | ||
| 8.4 % | With hydrogen; C21H30N6O6*Rh In acetonitrile at 50℃; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sodium ethanolate In ethanol | ||
| With potassium <i>tert</i>-butylate; lithium chloride In tetrahydrofuran at 0℃; | ||
| With sodium hydroxide In dichloromethane; water at 20℃; for 0.5h; Title compound not separated from byproducts.; |
| 13.043 % de | With lithium hydroxide monohydrate In isopropyl alcohol for 2.5h; Reflux; Overall yield = 91%; Overall yield = 1.430 g; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 80% | With benzyltri(n-butyl)ammonium chloride In o-xylene for 3h; Heating; | |
| 75% | With [{RhCl(C2H4)2}2] In o-xylene for 10h; Heating; | |
| 75% | In xylene for 10h; Heating; |
| With tributyl-amine; potassium carbonate In xylene at 130℃; |
